


New experiences, new feelings

by AnaBolena



Category: Supernatural
Genre: F/M, Feelings, First time having sex, Protective!Dean Winchester, Smut, first time blowjobs, some bad feelings, some good feelings, virgin!reader
Language: English
Status: Completed
Published: 2019-02-13
Updated: 2019-02-13
Packaged: 2019-10-27 13:02:05
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,190
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17767280
Author URL: https://archiveofourown.org/users/AnaBolena/pseuds/AnaBolena
Summary: The reader decides it’s time to venture into something she’s never done before, but her rushed decision leads to a disastrous outcome, that only her good friend -or maybe more- Dean Winchester can help solve.





	New experiences, new feelings

**Author's Note:**

> A/N: This story is a present for @waywardrose13 as a present for Galentine’s day!! She requested: “Dean x Virgin!Reader smut. I’m a sucker for those fics. They’re so sweet” I tried to make it as sweet as I could. I hope you enjoy this Rose. Happy Galentine’s day!!!
> 
> Written for @spnfanficpond Galentine’s Day Fic Exchange. Tagging @mrswhozeewhatsis
> 
> Also this is for @spnkinkbingo Square filled: Free Space.
> 
> A big THANK YOU and shoutout to @rachelladytietjens for her amazing and much needed help. Go follow now!

So here you are, sitting in the dark with a beer in hand. Hiding in the bunker’s kitchen in the middle of the night. Hiding from the world, from the disastrous date you just ran away from. Hiding from yourself in hopes to erase with alcohol the events of your fateful evening.

Listlessly you pick at the biggest tear in your fancy ripped jeans, anger flooding you as your fingers hook into the hole, tearing it all the way across your thigh.

“Shit!” you shout at the same moment the room becomes bright as day. Pushing away from your chair you stand in the blink of an eye, grabbing the gun hidden under the table and aiming at the large figure in the doorway. Your eyes take a couple of seconds to adjust and when they do, you see Dean with his hands up waiting for you to realize it’s him. “You scared the shit outta me!” You lower the gun placing it on the table.

“Sorry, Sweetheart! Hey, aren’t you supposed to be on a date right now?” he asks checking his wrist watch as he enters the room.

“I’m supposed to be lots of things,” you answer sarcastically, trying to tug the fabric of your ruined jeans back in place as if it would have some sort of magic velcro that’d stick it right back, your eyes roll when the piece of cloth falls back down.

“What does that mean?” Dean asks as he reaches the fridge.

“Nothing,” you sigh. “Can you get me one?”

Dean nods and then closes the fridge door turning around with two beers in hand, walking towards the table. He spots the tear in your jeans, and freezes. It’s Dean-the-Hunter who growls, “He do that to you?”

“No! I did it myself… My-My finger got stuck,” you assure him with a short smile, a genuine one, letting him know you’re fine before sitting back down.

Dean relaxes and sits down across the table, his eyes taking in the couple empty beer bottles resting on the table, and gives you an interested look as he says, “That bad, huh?”

“Yeah,” you breathe out. “Actually no,” you correct yourself after a moment. “The first part was great, you know?”

“Uh-Hmmm.”

“We even got to his place and all… And it kinda got hot,” you confess after a drinking pause.

Dean takes a swig of his beer, his eyes on you and with a raise of his eyebrows he urges you to keep talking. It’s not unusual, you venting your problems to him. Tonight he looks truly interested in listening to what you got to say, maybe because you’ve never talked about boy problems, probably because you’ve never had boy problems, but he doesn’t know that… Or maybe he does.

“But then I said something that maybe I shouldn’t have and of course, he said something that made me feel…” you stop and sigh.

“You know I can pay him a visit, right? Just gimme his address and I’ll make it look like an accident.”

You laugh and shake your head.

“Made you feel… sad?” he guesses and you shrug a shoulder. “Or we can both beat his ass and then I’ll cover our tracks.”

You smile at his attempt to make you feel better. “Nah, just. He made me feel like… Like I’m wrong!” You huff and sulk a bit in your chair. Dean’s hand reaches out to you and his fingers graze your knuckles across the table.

“And I’m not wrong!” you are quick to tell him. “I know there’s nothing wrong with being a-a-” Dean’s eyebrows drawn together and he gives you a quizzical look. “There’s nothing wrong with being what I am.”

“You tryn’a tell me you’re gay? “ he asks. You give him a surprised look.

Does he thinks you’re gay? Do you give you a gay vibe? You never thought about it before, but that lady did came up to you the other night and offered to buy you a drink, which you politely declined.

“You know I’m totally fine with it, right?” Dean adds and you put a pin in that thought to ask him later about the gay vibe.

“Yeah! I mean no! Ugh! I know you’re cool with it. But I’m not gay. I like men.”

“Ok, ok.” Dean nods, and the astonished expression he had on faded into a more content one. “What is it then?”

Your mind wanders as you try to find the words to tell Dean about your… condition, without using the actual words, not that is a bad thing, it is not, but this is how you’re feeling tonight. And the autoplay starts again right in front of your eyes… Matt and you moved from the couch to the bedroom after about twenty minutes - since you reached his place after finishing dinner - of a very heated makeout session. Everything was in full swing until his hand slid down the front of your jeans and found your soft spot. Your body reacted on its own and you slapped his hand away.

“I’m sorry I-I didn’t…”

He moves away from you a little, his eyes on you.

“I liked it. I swear!” you chuckled nervously.

He shrugged it off and in a moment his lips are back on your neck, making your eyes roll to the back of your head and his hand started his way south again until without even noticing it you slapped him, again.

“What is it?” Matt asked a little hasty.

“Shit! Sorry! It’s just I- I never-”

“You never what? Had someone finger you?” he laughed.

“Yeah, that’s exactly it. I never got this far before,” you admitted a little ashamed under his judging eyes. “I never let it get this far… with-with anyone.”

“Wait, does that mean you’re a virgin?” Matt stood up from the bed and had to hold on to his unbuttoned jeans before they could fall down his legs.

“Yeah, it’s not a big deal… I don’t want it to be special or anything. It’s just that I never got the chance- never let myself get the chance to get this far.”

“Jeez!” he sighed, pinching the bridge of his nose and letting himself fall back onto the bed, your body jumping with the momentum.

“What?”

“Yeah, no this-” he motioned with his hands between you and him, “-this is not gonna happen.”

“What? Why?” You raised your voice and yourself from the bed.

“Virgins, they get attached. I don’t do that. I don’t do virgins.”

Rage flooded your senses at his words and that stupid smug smile on his face as he believed himself better than you somehow. As if his dick would have some sort of super power or something that’d made you come back and beg for more. This time your body acted together with your brain and you punched him square in the nose.

“What the fuck?!” Matt grabbed his nose. “Why you do that?!”

“Because you’re a fucking asshole!”

“And you’re a fucking virgin! Get the fuck outta my house!”

“Hey, what is it? You alright?” Dean’s worried voice pulls you from the nebula that is your mind and maybe it’s because you’re angry or maybe it’s the almost 3 beers you already drank having some effect in you, or both things combined, but the words blurt out of you.

“I’m a virgin, ok?” you admit with annoyance.

“Oh, okay…I never woulda guessed,” Dean clears his throat and sits up, his hand leaving yours.

“What, you think it’s a bad thing too?”

Dean takes a second to get back to you, and it’s sort of reasonable considering what you just told him , but you are having none of that right now and you open your mouth to start the second argument, about the subject, of the night when he finally says something. “No! Of course not! It just. It never would occured to me to think you were-you are…Um that you never-”

“It’s a choice!” you say too strongly, taking a deep breath after to relax a little. “I never wanted the complications of sex while living the life…”

“And what changed?” Dean interrupts, his voice changed from the startled tone he had a minute before to a composed one, which made you stop and take a breath to calm yourself.

“What you mean?”

“Yeah, why this guy. You were planning on- with him. Why?”

“I… I honestly don’t know.” You take another chug of beer. “I wanted to get over with it and just do it.”

“Yeah, but why now?”

You think for a moment, trying to come up with the reason for it. “I guess I started thinking about it after the shifter that attacked me up a few months ago. I almost died! If you Sam hadn’t gotten there in time… He-”

“Hey.” Dean takes your hand in his. “We got there.”

“I know, thank you,” you smile and shake that feeling away. “So, after that experience I started pondering about life and I guess I wanted to do it before I die, because you never know and you know! I wanted to know what it was like… It’s the stupidest reason, I get it now.”

“It’s not. It seems like a good reason to me,” Dean shrugs. “But that guy sounds like the biggest douche and you still haven’t told me why him?.”

“Oh right. I dunno, he was there. We’d been texting for a while and he seemed nice. He never sent a dick pic!” you snort a short laugh. “ And besides, he was only one to ever show interest in me. You know I’m not one to flirt much when we go out and heads never turn when I walk into a room. But Matt he-he bought me a drink and asked my number.” You sigh and finish your beer, licking your lips and nodding silently as an involuntary movement, agreeing with nothing or everything that happened tonight.

Dean scoffs and you look up to meet his eyes. Beautiful green eyes, kind under the white light of the kitchen that makes his freckles stand out. Your eyes roam his face, taking in every inch of it and the small smile tugging at the side of his plum, pink lips. “That’s not true,” he finally says.

“What’s not true?”

“You make heads turn, only you don’t notice, you never notice. And guys don’t come up to talk to you because you give off a really intimidating vibe,” he chuckles and you join in.

“I guess I have a really bad bitch resting face.”

“Yeah, no offence!”

You laugh and wave him off.

“Me and Sam, we know you. But that face… I mean you’re still beautiful, you always are -he licks his lips- but most guys are assholes and feel intimidated by powerful powerful, gorgeous women”

“And you don’t?”

“Nah, your bark is worse than your bite.”

“So you think I’m gorgeous?”

Dean smiles, white teeth on display. “So you got that?”

“Well, of course. I always thought you thought of me as cute or as a fucking badass hunter-” you laugh.

“Super badass!”

“But beautiful and gorgeous?”

Dean shrugs in response.

“You’ve thought of me…sexually?” The moment the word leaves your lips you feel a vibration running down your arms and legs and the tingling on your nipples.

“Yes.”

Your eyes widen at his response. “Okay, that was a fast answer.” Looking down you notices his hands never left yours and now his thumb is rubbing in soft circles as middle finger and thumb from his other hand hook around your wrist. You swallow down and clear your throat. “You know that love- you clear your throat again- love has nothing to do with sex, right?” You don’t want to overthink it, but this whole exchange most likely would lead to two outcomes and you wanna be sure he knows exactly what you want. Dean nods and licks his lips again, his smooth looking tongue lingering on his lower lip, leaving a glistening layer behind. Of course he knows that, his conquests tend to be one night stands. “That’s what I was wanted, no love involved.” Dean leans over the table, getting closer and you do the same, lowering your voice as you do since he’s so close. “But now there’s a big difference…”

“And what is that?”

“I- you sigh, goosebumps prickling all over your skin as his hand travels up your arm- “I didn’t really knew Matt. I coulda gotten up and left afterwards and that was it. It was over. I woulda never had to see him again. No awkward moments or new feelings added to the relationsh-”

With his thumb on your lips Dean silences you. “Look, you can get up and leave afterwards. We’ll pretend it never happened, if that’s what you want.” His green eyes drop from your eyes to your lips. “We can stop now, if that’s what you want.” He pauses to take a deep breath. “And if new feelings are awakened, then we’ll deal with them.” His long fingers slip behind you ear as he cup your face and his eyes meet yours again. “I like you, Y/N. I really do.”

You breathe a laugh. “I like you too.”

“Good,” he nods. “You want this?” he whispers the question so close to your mouth, his warm breath moisten the fuzz above your upper lip.

The proximity of Dean’s body to yours makes the air come in and out of you in short pants, your breathing so shallow you start to feel like you might faint. Inside your ears the drumroll of your heart is all you can hear. Do you want this? Of course you want this! You wanted this with Dean ever since you first set eyes on the seasoned hunter. Although you never thought he would ever want anything to do with you. You never considered yourself other than pretty, a girl next door kind of pretty, and certainly not the Dean Winchester type. And every moment you spent with him for the past 4 years allowed you to know him as a person and not just as the handsome, seductive, flirty, kissable man he was. You knew how friendly and kind he was, you got to know the good humoured and lovable interior that hid under the strong armour, and that made you want him more than anything.

Do you want this? Pffft!

“I want you,” you say before claiming his mouth in a searing kiss that he’s quick to reciprocate.

Both of his hands are now around your face and he pulls you to stand up with him, but he is taller than you and you are obligated to clumsily climb onto the table, one knee at the time, your own hands leaving his body to help you hoist yourself up from the ground and kneel on the hard surface. Dean helps you with one hand to unfold your legs from beneath your body, so you don’t fall off the table, until you sit in a more comfortable position right in front of him, your knees now closing around his hips and thighs as Dean ducks his head to kiss you again. His fingers card through your hair and at the same time dig on the exposed section of skin exposed on your side as your shirt rode up from all the movement, causing you to jump in surprise before remembering that most people have two hands and can use them separately.

You smile at your own reaction and Dean takes it as you being happy with what’s going on, which you are of course, but that leads to a confession from him. “I know I never thought this would ever happen either.”

What was that supposed to mean? Did he want you from the beginning just like you did him? That was so fucking cliche, he wanted you and you wanted him - with a slight chance of a crush, not really that kind of love because you loved the guy, just not quite like that. But what if he loves you like that and you realize you won’t ever be able to? What would happen then?

His hand kneading you breast under your shirt pushes every logical thought out of your mind. You hand crosses the harsh barrier of his belt and the waist of his jeans causing Dean to groan as your fingers wrap around his hard member, applying a hard pressure around the head. You might have never done this before but you’ve watched plenty of documentaries about it on that interesting online page you found, pornhub, to know the theory. Dean’s hips thrust forward into your hand and he kisses your neck, his mouth leaving a damp trail around your throat. His fingers leave your hair, not before closing as a fist around it and pulling your head back to allow himself more room to explore your neck and chest, and start tugging at your braided leather, D-buckle belt that you keep for special occasions. This time, unlike with Matt you don’t slap his hand away. On the contrary, you help him by opening your legs wider to make room for him to get closer to you. You gasp loudly as his warm digits reach your heat and you both discover how wet you are.

“Fuck!” he sighs against your ear before pushing his teeth to your skin, just strong enough to let you know he could do much better than that.

The circles that are being drawn around your clit cause a fire in the pit of your stomach that spreads down to your groin and you know you’re going to come but it has never been this intense when you’ve done it yourself. Dean pulls the cup of your bra down, and with the tip of his thumb and forefinger rolls your left nipple, and that’s enough to make you explode. A blinding light blasts through your body, boiling hot and freezing cold at the same time, as if an angel just came down from heaven and blasted your soul to hell, where it surely belonged.

Dean continues rubbing, only more gently. You take his wrist to stop him and he complies immediately. Panting you look up at him, his lust blown eyes staring back at you and he waits, breathing heavily. He waits for you to allow him to go on.

“D’you- you have protection?” you ask, swallowing around a dry mouth.

“M’ room.” He moves away from you and pulls your hand from inside his jeans where it remained idle from the moment he started using his, and leads the way towards his room.

Neither of you have reached the bedrooms’ hallway so fast, ever. When you get to his room, Dean grabs you by your nice shirt, the one you just realized you wore and you stop him from tearing open to get you undress.

“Sorry,” he apologizes breathlessly.

Pushing your fingers away, he starts to unbutton it. Taking his own damn time with each damn button. The butterflies in your stomach flutter harder and faster with every inch of skin that a newly opened button uncovers, and he surely notices because he starts kissing you again, distracting you completely from it. Well, almost. Dean Winchester’s hands are undressing you, it’s impossible not to concentrate on that. Your tongue meets his to dance at a slow lustful pace and you moan into his mouth just as the soft fabric of your shirt glides off your shoulders and arms, pooling behind you with the softest thud.

He wraps his arms around your back to unhook your bra and your lips leave his when you finally move away to remove the undergarment from your upper body. “God, you’re fucking gorgeous!” he sighs, his mouth on your body next with his worshiping all of you at once.

You push him off of you and he freezes on the spot, thinking he might have done something that made you uncomfortable, you smile and push his flannel off his broad shoulders, tugging at the hem of his dark t-shirt once the first of his rare only two layers outfit falls to the ground. Your hands roam around his hard chest and soft stomach and they only stop when your lips latch to his right nipple. Dean growls in pleasure and his hands land on your head, fingers tangling around your hair keeping you in place and then without prior notice he pulls you off of him.

Pressing his chest to yours, Dean forces you to walk backwards until the back of your legs meets the edge of his bed. His arms wrap around your waist and while lifting you up in the air he throws himself to the bed with you on top of him. As soon as you land he sits up with you straddling his lap, both of you naked from the waist up. You love the way his chest feet against you, his warm, creamy skin against yours. Your lips meet once more and you grind down onto him, his hardness tucked inside his jeans still, pressing in between your legs, igniting the sparks that precede the electric storm. You cry out into his mouth and Dean moans your name.

He lowers you onto his legs and slowly removes himself from underneath you. He takes off your jeans and underwear, not even noticing you’re wearing your fanciest pair; same way with your matching bra that now rests on top of the pile of discarded clothes by the door, stopping on the way to unzip your ankle boots and toss them over his shoulders, and then again a few times when your feet got caught in the ornamental holes of your jeans. “I fucking hate ripped jeans!” Dean sighs when he finally pulls them off.

He lowers himself, finding your thighs with his lips, pushing your legs apart to settle in between them. You close your eyes and take a deep breath, feeling his tongue discovering every fold, every crease of your sex, but soon it becomes too much and your push him away.

Dean kneels on the bed, pulling at his own belt and undoing his jeans. With some difficulty he stands and toes his boots off after loosening the laces. And right in front of your face he finally kicks to rid of his jeans and boxer briefs to reveal his erect cock to you. You swallow down, you’ve never seen one face to face, but still you know exactly what to do and you’ve never wanted to put something into you mouth so badly. Gently licking the head you grip around the base, feeling the throbbing on your palm, and you slowly take him in, deeper and deeper until the gag reflex shows up and he pulls you up.

“You just need more practice,” he says pushing you to lay back again. “We’ll work on that next time.”

Next time? He wants there to be a next time!

You position yourself with your head on the pillow and wait as Dean looks for a condom on the first drawer of his dresser. You give him a questioning look when he comes back with the square wrapper and a bottle of lube.

“It’s not really necessary, but I don’t wanna hurt you.”

“Oh, okay. Thank you,” you awkwardly and timidly say as he rolls the condom down his length and then squirts a good amount of lube around himself.

Dean chuckles at your expression and jumps on the bed so swiftly you don’t even notice when he placed his legs in the middle of yours or when he started hovering over you. His hot skin brushes over yours and his breath fanning over your neck and chest let you know sweat already gathered all over your body. He leans into his elbows on both side of your head.

Your chest starts raising and falling too rapidly, the reality of what’s about to happen hits you. You never thought you’d be this nervous and of course you never thought you’d be doing it with Dean. What if you’re not at his level, or you don’t perform the way he likes. Or what if it hurts, really hurts. He seems big, you choked on him, but then again, you’ve never done that before.

“Look at me,” Dean interferes with your incessant internal inquisition. Your eyes flutter open and the tranquil expression painted on his face is enough to calm your nerves down for a minute. “You’re okay. Breathe,” he commands and you comply filling your lungs and letting the air escape slowly and steady. Smiling down at you, he caresses your cheek and kisses you one more time. “Let me know if you don’t feel like keeping going, ok? I promise it won’t hurt too much.” You nod and allow him to slide one hand in between your bodies, in order to line up his cock to your entrance, and as lazily and languidly as he’s able to Dean pushes in, gauging your reaction.

“Oh my god!” You gasp and your eyes open wider than ever.

It seems as it you’re being slashed open but at the same time it’s nice and sensually pleasing. Dean’s cock opens a path that’s been closed for so long and he sinks deep, so deep, that it feels like he will never get to the bottom but he does and he stops there. His chest fills almost crushing you and you recognize the bliss on his face. His features transformed with a mix of delight and agony as he wills himself not to move to let you adjust to him.

Staring into his eyes you circle your hips, fearfully at first but once the slight unpleasant feeling of muscles being strained disappears you become confident and move with purpose. “Shit!” He shuts his eyes tightly, meeting your lunges until he gradually takes the lead, pulling out almost entirely only to thrust back in, bottoming out. Dean’s eyes flutter open when your voice becomes louder and he dares to move faster and go a little harder. Causing you to cry out and he stops immediately. “I’m sorry! Am I hurting you?”

“No! Fuck! Don’t stop!” you beg and Dean complies.

The friction of his pubic bone on your clit forces a new wave of arousal to cascade from your core and Dean moans in your ear, quickening his pace. When you reach your peak again he has to stop moving, holding his own release in. But after you recover he takes one of your legs and paces it around his hip and you quickly do the same with the other one. His arms wrap around your shoulders and back and he starts going faster and harder that before, lifting your upper body from the bed with his. The arm around your shoulder moves and he strokes your hair, pushing a few strands behind you ear to move it away from your face so he can look you in the eyes. He smiles earnestly, his eyes scan every inch of your face in adoration, his teeth bite over his lower lip, containing the grin threatening to form. Suddenly underneath his eyes you feel naked, beyond your physical form, the way his eyes bore into you cause your heart to jump faster inside your chest. A sparkle gleams between you in that moment, impossible to ignore, your chest feels tight and your lungs burn as you realize you’re not breathing and you draw a deep breath.

“You are so beautiful,” Dean declares before his lips claim yours again. The new position allows him to hit the precise spot inside you that makes you thrash almost instantly. This time he’s not able to hold it and his movements stutter as he comes, wailing in pleasure as he shoots his load inside you.

Some minutes go by and you’re finally able to detach from each other, whining a little when the sweaty skin peels apart.

As you lay there in silence, acknowledging the burn from your insides from what you just did the wheels start turning again inside your head, and as much as you try not to think and overthink about it, all you can focus on is the look he gave you, the moment you two just shared. So intimate, so pure and perfect. What does that mean. Does he feels something else? Do you?

Dean says nothing, all you can hear beside your own heart are his heavy breathing.

Asshole Matt was right all along. This is just in your mind. You got attached and any friendship or possibility of a future meaningful relationship with Dean will be from now on doomed.

“Hey!” Dean’s soft voice pulls you from the dark cloud fogging your mind. “Remember we said it wouldn’t be awkward?” You nod and turn your head to look at him. He licks his lips. His fingers move to push some hair off your sweaty forehead, and then traver down your face and jaw, reaching your clavicle, raising goosebumps on the go and making your inside throb with want once more. “Talk to me?”

You push yourself up a little and roll to rest on your side, facing Dean completely. “I’m not sure how I’m supposed to feel. My head is in a turmoil of mixed feelings. But I don’t regret this. I don’t regret doing it with you.”

A sad looking smile tugs at the side of his mouth just as if he wished you’d said something else, something different. “That’s okay.”

“Do you know…how you feel about this?”

“Yes,” he whispers his answer, his fingers carrying their tour down your body. “But I knew beforehand. I’ve known it for a while now.” The tip of his index finger delineates the outline of your areola, you gasp. A hunger reawakening inside you.

“Dean,” you sigh.

“Don’t over analyze it. Let yourself go. Enjoy, explore the feelings. You don’t have to decide how you feel right now.” With his other hand he struggles to remove the used condom and tosses it to the floor before crawling on top of you, the wet and anew swollen head of his cock poking on your thighs.

“Dean,” you cry out his name.

He moves a little and positions himself with his legs around your hips and his length in between your legs, grazing your enlarged and sensitive clit. Your fingers clasp around his biceps as you try to make him stop. 

“You really wanna talk about your feelings?” he asks. You start feeling light headed and unable to speak as his grinding fulfills its mission. “Okay then.”

“No!” you say with both hands on his hips to stop him, digging the tips of your fingers into his flesh when he doesn’t do it right away. You push him off of you and with a confused look Dean complies, laying next to you on his back. Quickly you climb to your knees and straddle his hips. “I wanna explore them.”


End file.
